It helps if one knows the context in which he addressed that particular church. Obviously women in church were not perfectly silent; they participated in prayer and song just like the men. And as for ‘teaching’, I’m pretty sure St. Paul meant in the context of ‘proselytizing’. There were Gentile and Jewish women who, I had read, came into the gatherings and disrupted the services in trying to ‘shut down’ Christian teachings, and St. Paul didn’t want the Christian women to get into rebuttals etc.
Everybody likes to make out St. Paul as this ‘anti-wimmen’ kind of "Let’s keep the men firmly in charge’ guy who took the beautiful “all are equal” message of Jesus and firmly stamped “MEN ONLY” onto it, but St. Paul was a Roman citizen. Rome may have had the whole "Paterfamilias’ thing but for a Roman citizen of his time, the average woman had a pretty high rep. The average Jewish woman too may not have had the kind of ‘court sanctions’ that women have today but she was, re Proverbs, seen as a helpmate more often than a chattel. He also studied with and had high respect for the Rabbi Gamaliel, whose own teachings were inclined to favor women in many ways.
It is not really so much that ‘teachings change’ --with the idea that “men bad then, get better now” but that with careful study, we see that teachings can develop.
It’s more like, “The teachings are still the same, but our understanding of WHY it was said and what it might have meant might change.” For example, some people back in the 17th century might have taken it to mean ‘women not capable’ because that whole century, with societal upheavals in Europe and an imperfect understanding of 1st century Rome and Judea --brought about often by Protestants ‘reading Scripture by themselves’ and understanding words to mean ‘then’ what they meant in AD 1630 or so–didn’t get the full context or story. Fast forward about 400 years and with more information available and less inclination to insist that one’s ‘vernacular’ Bible words and attitudes are the same as those of AD 2019, and we ‘get’ that St. Paul was NOT ‘dissing women’ at all.